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Allyl bromide → (3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917360
ノート
印刷プレビュー

反応式

HRID 1917360 の反応式
[C:1]([O:5][C:6]([C@@:8]1([CH:22]=[CH2:23])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24](Br)[CH:25]=[CH2:26].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([C@@:8]1([CH:22]=[CH2:23])[C@H:12]([CH2:26][CH:25]=[CH2:24])[C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 67490859(3R)-5-Oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 67490978(3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester収率 50.6%

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(3R)-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester (236.0 mg, 0.75 mmol) and allyl bromide (271.6 mg, 2.24 mmol) were dissolved in tetrahydrofuran. A 1 M solution of lithium hexamethyldisilazide in tetrahydrofuran (1.12 mL, 1.12 mmol) was added dropwise in a nitrogen atmosphere at 0° C. After stirring for 1.5 hours, a saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (10% ethyl acetate/hexane) to give 135 mg of the title compound as a colorless oil.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-33243f2c2711457597a11d4f4ba6eb54
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08618094B2

反応ノート

読み込み中…

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